How do you know the choices you are making in your WIP are the right ones? I find myself second guessing a lot of the choices I'm making this go-around.... and then second guessing my indecisiveness. I don't know how to get past it
To an extent you won't ever know, and the challenge is being comfortable with that. Usually a bit of time away from it will lead you to a more concrete decision. If not, break it down into pros and cons or even just an explanation of your rationale. Having to advocate for and against a decision in writing might expose things you haven't considered.
Give yourself permission to fail. That's what I do; I give myself permission to fail. I completely know that feeling you're talking about, and I think it's all part of the writing process for a lot of us. Just remember we can have endless attempts to get it right. Sometimes that seems to happen right away. Other times words come slower and we can almost panic over the decisions we have to make. I've been in these places and all across the spectrum. One writing tip I was given is to always choose Option C. If you're unsure about a decision you after to make in your story, there is usually an Option A and an Option B you are thinking about. If you take those off the table, what else is there in terms of the story or character direction? And then sometimes that's the best way to go. This little piece of advice has really helped me out quite a bit. Worth considering.
All any of us can do is trust our instincts and hope it works out. Unless I recognize a problem or potential problem, I just go with what I want to say, what my gut tells me is right. I've read a ton of novels, I've read a ton of writing advice and I've gotten better at this writing thing over the years. I know you've done the same. Our instincts aren't perfect and probably never will be, but they're honed. Believe in yourself. And if you can't choose because there's a potential issue with either option, try what @deadrats was talking about with option C. That sounded pretty smart to me. I've done this on occasion myself, especially with wording. If I don't like either way I've written the sentence, I start from scratch.
This. Trust your instincts. If it doesn't "feel right," give it more thought. It's like puzzle pieces coming together, and if one piece does not seem to fit, you have to search your mind for another piece. I've found myself in this position many times. It's like - would this character really act this way? How would he act? What reaction fits with his character? Then do the mental work to find what fits. When it's right, you know it.
I agree very much with all the responses here - and I'd like to add that the question is vague, especially the word "right". Writing is not math. There isn't one "right" answer. In writing, 1 + 1 can be 2, or 3, or pi. What matters isn't that you get the "right" answer, but that your answer -- whichever one it is -- is convincing enough to become right. The important thing is having the courage of your convictions to make your answer the right answer, and the only answer. Let's suppose that (for instance) your character is the classic adventurer, trapped in a labyrinth (aka Theseus and the Minotaur). Your adventurer comes to a a T-intersection. On the right, he can hear waterdrops dropping, and a faint sizzle. On the left, he can hear squeaks and scratches on bare stone. That's all he has to go by. What's the right answer? He doesn't know. The reader doesn't know. You have to know -- and you have to know what's on both sides, and give your character a convincing mental process by which he decides what to do. Maybe he tries to sneak a better look at both sides, and then decide. Maybe he tries to fight his way out. The point is, it's up to you. Good luck